SLEEPY HOLLOW COUNTRY CLUB – A COURSE TOUR & APPRECIATION
Scarborough-on-Hudson, NY – C.B. Macdonald, Seth Raynor, A.W. Tillinghast
Full disclosure: I love this place. Sleepy Hollow is, quite simply, one of my favorite places in the country to play golf. Exceptional golden age architecture, spectacular views, exciting shots, fabulous conditions — Sleepy Hollow has everything a golfer could want. And to top it off, Sleepy Hollow is the course that sparked my interest in the work Charles Blair Macdonald and Seth Raynor, and subsequently my love for golf architecture generally. So I’m biased.
And of course, I’ve been wanting to do a photo tour of Sleepy Hollow for quite some time. As with my tour of Old Town Club, Sleepy Hollow’s recent near miss on Golf Digest’s Top-100 list provided a perfect impetus and incentive to pull this tour together and shine a bit of a light on a place that, for me, is ranked about 100 spots too low.
The photographs you see below were taken over the course of two visits to Sleepy Hollow (which is the reason for the differences in light, course conditions and pin positions).
I hope you enjoy the tour.
SLEEPY HOLLOW COUNTRY CLUB
Sleepy Hollow was built on the 338-acre Woodlea estate, which the club acquired in 1911. C.B. Macdonald designed the golf course, with Seth Raynor on the ground as engineer, and the original 18 holes were completed that same year. In the late 1920s, AW Tillinghast expanded the course to 27 holes, creating several new holes for the 18-hole “Upper” and 9-hole “Lower” courses. Via the passage of time and the intrusion of several interim architects of more modern vintage, the course lost touch with its golden age roots for a period. George Bahto and Gil Hanse were brought in to restore the course’s rightful Macdonald heritage.
The result speaks for itself. In its present form, the main course at Sleepy Hollow is rife with beautiful interpretations of many of the Macdonald templates, including Redan, Punchbowl, Double Plateau, and one of the most gorgeous Shorts this side of Fishers Island. While the property has been owned by Colonel Eliot Shepard and William Rockefeller, and the course has been worked on by some of the great architects in golf, including Tillinghast and Hanse, Sleepy Hollow today stands clearly as a shining example of CB Macdonald’s design tenets and as a fitting monument to George Bahto. Quite a lineage.
No tour of Sleepy Hollow is complete without at least a brief discussion of its magnificent clubhouse. Some of the best courses in the country are identifiable by their clubhouses alone, and in a few instances — Winged Foot, Oakmont, Myopia Hunt, Ridgewood, and Shinnecock, to name but a few — they become iconic in their own right. Sleepy Hollow’s is one such clubhouse.
Looming high above, the clubhouse, designed by Stanford White in 1893 as the manor house, is the first thing the golfer notices about Sleepy Hollow upon entering the gates, and it provides quite the first impression. As the long entrance road makes way up toward the building, the loping route provides views of several holes on the lower course, the driving range, the stables, and the many rock formations that remind the golfer that he’s in Westchester. But all the while, the presence of the massive clubhouse dominates.
The entrance road culminates at the south face of the clubhouse, seen in the photo below. The parking lot is in the rear, to the right.
The clubhouse has been the scene of several television shows and movies, and has hosted countless events. And with views like this from its spacious lawn, it’s easy to see why.
It is a beautiful building and a fitting way to begin a day at Sleepy Hollow.
The Scorecard, Logo and Haunted Bridges
A golfer senses a theme at Sleepy Hollow. The club has named each of its holes in reference to Washington Irving’s story, which was set in the surrounding hills. The course itself stretches to 6880 yards and plays quite pleasantly at 6377 yards from the white tees (which I use for this tour) to a par of 70.
The club’s logo of the Headless Horseman, likewise taken from the Irving story, is one of the best in golf.
Finally, the Haunted Bridges, encountered on the 3rd, 10th and 16th holes, appear to have been built by Irving’s contemporaries and provide a unique and fitting touch.
THE GOLF COURSE AT SLEEPY HOLLOW
Hole 1 – “Sunnyside” – 406yds – Par 4
There is no more enjoyable way to start a round of golf that from a first tee that sits in the shadow of the clubhouse, as is the case at Sleepy Hollow. The Hudson river just peeks out above the treeline, giving the golfer a small taste of what’s to come.
The first hole is a downhill dogleg right which, while tree lined, has a more generous landing area and more room to work the ball than it first appears. The ideal position is the left half of the fairway.
The first green is of a good size, but the bunkering on both sides and the visually deceptive framing bunker short left make for a challenging first iron.
The fairway runs seamlessly into the green, allowing for the ball to be run on to the putting surface, but the green slopes up from front to back. The deep Macdonald bunkering is felt immediately.
The view back up the first hole — steeper than it appears, and a solid start to what will become a memorable round.
Hole 2 – “Outlook” – 321yds – Par 4
Reminiscent of the first hole at Myopia, the second hole is a short, uphill par-4 defended by a relatively severe, well-protected green. The “eyeglasses” bunkers short of the fairway are not in play, but make for an appealing visual effect.
The approach to the second green will almost always be from an uphill lie, making for frequent short-right misses. This deep-and-steep wraparound front-right bunker is waiting to catch those misses.
The climb to the second green at Sleepy Hollow is the first point on the course where the golfer is treated to both the stunning views of the Hudson River . . .
. . . and to the sight of Sleepy Hollow’s one-of-a-kind walking bridges. This is the point in the round where the golfer knows, beyond a doubt, that a special day awaits.
Hole 3 – “Haunted Bridge” – 153yds – Par 3
Aptly named, the third hole may be the best par 3 among the standout collection of one-shotters at Sleepy Hollow. Played over a deep ravine to a green elevated just enough so that the golfer cannot see the entire putting surface, the third provides one of the most exciting tee shots on the front nine at Sleepy Hollow.
The way in which the land was sculpted and the third green was benched into the hill will appeal to even the most jaded GCA enthusiasts.
To access the green, the golfer crosses the Haunted Bridge for the first time. Simply beautiful.
Hole 4 – “Brom Bones” – 404yds – Par 4
Cresting the hill after putting out on the third green, the golfer is afforded a wide view from the fourth tee over a large, open section of the golf course. The fourth hole plays out to an open fairway that dips down, then crests a small rise before arriving at the green.
Longer shots may clear the rise, offering the golfer an unobstructed view of the putting surface. For those that do not, an aiming marker is provided behind the green.
A precision approach shot is required, as the fourth green is well guarded with deep bunkers, and is itself riddled with undulations, allowing for difficult pin positions.
Hole 5 – “High Tor” – 403yds – Par 4
Playing back in the direction of the fourth tee, the fifth hole plays over the rise in the fairway (which is an easy carry for all players), then drops quickly before again rising to meet the green. The view from the crest of the rise is spectacular.
The encroaching bunkers, which begin well short of the fourth green, provide for an added challenge on the player’s approach. Shots that come up short are in danger of rolling several yards back down the fairway.
Approaches that come up short face this shot, with only the green (with its false front and varying internal mounds) and the pin in view.
The fifth green. No words necessary.
Hole 6 – “Headless Horseman” – 458yds – Par 5
The first three shot hole at Sleepy Hollow is short on the card but plays longer, thanks to the hill that must be climbed before reaching the second fairway. Aggressive, longer hitters can carry the steep, mounded wall but many players are better off simply laying up short of it. Right is dead, and the massive grass bunker on the left side of the hill just wishes it was dead.
Once reaching the upper tier of fairway, the golfer must contend with the principal’s nose bunkering, which sits smack in prime lay-up territory some sixty yards short of the green.
The sixth green slopes substantially from back to front — approaches that end up beyond the hole will result in a very tricky putt back down to the hole.
Hole 7 – “Tarry Brae” – 193yds – Par 3
In your author’s humble opinion, the best downhill reverse-redan hole in existence.
The steepness of the green from high left to low right is so pronounced that balls routinely roll for 30 seconds or more as they funnel down toward the pin. A wonderfully exciting hole to play.
Hole 8 – “Sleepy Hollow” – 439yds – Par 4
The eighth hole begins the stretch of holes that were originally laid out by Tillinghast, and which are, for the most part, on a flatter, narrower portion of the property. Nevertheless, the rolling terrain provides for many interesting shots, as first seen on the par-4 eighth hole. Off the tee, the preferred result is the left side, but the partially hidden low left fairway bunker must be avoided. A large mound in the right half of the fairway can scatter balls in any direction.
The eighth green is set perfectly among the hills and rocky outcroppings. A false front repels indifferent approaches.
The eighth green, with the eleventh green complex visible behind.
Hole 9 – “Katrina’s Glen” – 377yds – Par 4
The ninth provides a generous landing area for tee shots, but balls that end up short and right will face a blind approach to a small, well defended green.
Tee shots that find the high left side of the fairway will have the preferred look down the center of the slightly elevated green.
As shown in this photo, missing left is bad, but missing far left is awful. Note the many appealing pin positions in the rippling green.
Hole 10 – “The Lake” – 136yds – Par 3
As noted above, the 10th is probably the “worst” of Sleepy Hollow’s four one-shot holes, which should tell you everything you need to know about the high quality of the quartet that the course presents.
The only hole at Sleepy Hollow with a true water hazard (the 12th has a small stream crossing it), what you see is what you get . . .
. . . but it sure is pretty.
Hole 11 – “Ichabod’s Elbow” – 371yds – Par 4
The offset teeing ground of the eleventh hole, benched into the side of the hill bordering the property, creates a soft dogleg right which favors a cut first shot. While there are rugged, wooded areas on both sides of this hole, even bad shots are typically found and played.
The eleventh’s key feature is its elevated green and surrounding green complex. As you would expect, the elevation of the green makes the bunkers much deeper and much more penal as a hazard.
The green is also one of the most undulating on the golf course . . .
. . . and this raised section in the right rear of the putting surface makes for both some interesting putts and some impossible recoveries from misses left.
The wonderfully constructed eleventh green complex, as viewed from the left side.
Hole 12 – “Double Plateau” – 513yds – Par 5
The second and last par 5 at Sleepy Hollow, the twelfth winds left between the varied hills and mounds that mark this section of the golf course. This hole was one of the most modified by Bahto and Hanse, and it is safe to assume that Macdonald would approve.
The hole is reachable in two by longer players capable of positioning their tee shots in a spot that allows the dogleg to be negotiated. Those laying up must contend with a small stream that winds across the fairway a few dozen yards short of the green and down the left side of the fairway.
The three-tiered double plateau green is exceptionally built and, while severe in spots (as it should be) it is also large enough to accommodate accessible pin positions. The steep fairway-cut slope fronting the green adds another layer of challenge, especially to front pins.
A look back down the twelfth hole.
Hole 13 – “Andre’s Lane” – 384yds – Par 4
The thirteenth marks the golfer’s return to the area of the course originally developed by Macdonald, and it’s an excellent hole. A wide, gently inclined fairway slopes gently from high left to low right, and while a line up the left side is ideal, it also confronts two fairway bunkers and a cross-hazard. A line up the right is safer, but not only risks caroming into the rough, but also requires an approach from a less-than-ideal line over perhaps the deepest bunker on the course. At Sleepy Hollow, such risk/reward decisions are confronted on a continual basis.
The raised thirteenth green complex is one of your author’s favorites. In addition to the extremely deep front right bunker, the complex features a pot bunker cut front left, along with a large expanse of fairway cut that extends well to the left of the green before culminating in a kick-slope that tumbles to the putting surface. This unique setup allows for players to play safely away from the righthand bunker and either benefit from the built-in slope or to putt from above the left side of the green. An old stone wall frames the rear of the green. A wonderfully designed feature.
The thirteenth green as viewed from the fourteenth tee, showing the large area of fairway cut grass. Putting from up there is both challenging and fun.
Hole 14 – “Homeward Bound” – 378yds – Par 4
Yet another aptly named hole, the fourteenth tee is set at the eastern corner of the property, the farthest point on the course from the clubhouse, and the next five holes stretch across the property and return the golfer home. The tee shot on the fourteenth appears simple but is deceptively complex. From the tee, the righthand bunker juts into the rising fairway. But this small hill not only obscures the green . . .
. . . but hides a similar, though larger, lefthand cross bunker that sits just beyond the high point of the fairway. The firm conditions and the now-downhill slope of the fairway will carry most balls that crest the hill left of center into this bunker.
The fourteenth culminates in a narrow, deep green – one of the smallest on the course. The green slopes relatively gently from front to back before abruptly ending and falling several feet to a right rear bunker or the rough below.
From the right side, the golfer is treated to a long view of the green, the multi-tiered bunkers that separate the fourteenth and fourth greens, and the ever-present rocky surrounds of Sleepy Hollow.
Hole 15 – “Punch Bowl” – 437yds – Par 4
The fifteenth is your author’s favorite hole at Sleepy Hollow, and it is fantastic. An Alps/Punchbowl amalgamation, the combination of features found on this hole are unique in my experience, and together, they combine to form one of the most exciting, rewarding golf holes that I have ever played. From the slightly elevated tee, only the first 400 yards of fairway are visible to the golfer, along with the right fairway bunker.
The fairway is generous but canted rather substantially from high left to low right. The left side of the fairway is ideal, and anything right of center runs a high risk of catching the right fairway bunker.
The long approach shot is entirely blind, as the green sits some 20-30 feet below the fairway. The perfect shot is played out over the right hand bunker, left of the aiming flag. As the golfer crests the fairway . . .
. . . he is rewarded with the breathtaking view of the punchbowl green, with the sixteenth green behind and the Hudson River valley far below.
Looking back, the proper route to the green is revealed. One could never tire of playing this magnificent hole.
Hole 16 – “Panorama” – 150yds – Par 3
One of the most beautiful one shot holes in the country, the Short at Sleepy Hollow plays back over the gorge that was first confronted on the third hole to a green ringed almost completely by a trench bunker. The club has wisely removed all of the trees that once marred this spectacular view.
Gorgeous from any angle, the sixteenth’s views hide a surprising amount of slope within its putting surface.
The golfer again crosses the Haunted Bridge over the gorge on his way to the sixteenth green. The way that the third and sixteenth holes were laid out over this terrain is a brilliant example of an architect making the most of a unique but difficult feature.
Hole 17 – “Hendrik Hudson” – 433yds – Par 4
The seventeenth plays shorter than its yardage, as tee shots will roll forever. Given the heavy cant of the fairway from left to right, however, care must be taken to properly place one’s tee shot or risk it rolling into the right rough for the cluster of fairway bunkers which are just out of view below the crest of the hill.
The cluster of righthand fairway bunkers, as well as the extended fairway, are revealed as the golfer descends the seventeenth fairway. The firm, fast conditions make these bunkers play far larger than their footprint.
Level lies on approach are few and far between, making this narrow, bunkered green a difficult target. The fairway runs seamlessly into the front of the green, however, leaving the option for a ground attack open.
The greenside view of the long downhill penultimate hole.
Hole 18 – “Mansion Rise” – 401yds – Par 4
While the seventeenth plays shorter than its yardage on the card, the eighteenth, leading back up to the iconic clubhouse, plays much longer than its listed 401. While tee shots up the left side of this relatively narrow fairway will bounce down into ideal position, the lefthand fairway bunker must be avoided, as it makes reaching the green (or anywhere nearby) a virtual impossibility.
The beautiful approach shot with the clubhouse directly behind the green (and, often, the lunch crowd observing play) provides one last pleasant memory of a golfer’s round. While getting up and down from a left miss is tough, missing right can lead to a 30 yard uphill pitch.
The green, following the slope of the land, is pitched substantially from back left to front right. Putting back to a front pin is a challenge.
Like the first tee, the final green at Sleepy Hollow sits mere steps from the clubhouse.
Sleepy Hollow is a must not only for any fan of CB Macdonald, but for anyone with a love for golden age golf architecture or just a love of fun, exciting golf. Head Professional David Young, Superintendent Tom Leahy and the club’s members are rightfully proud of their golf course and have acted as outstanding custodians of this treasure. Soon, as more raters see Sleepy Hollow in its current form, it will assume its rightful place on every top 100 list there is. But until then, it remains an underrated gem that everyone should try to see at least once.
I hope you enjoyed the tour.